WO2003074011A1 - Utilisation cosmétique de la phytosphingosine comme agent amincissant et compositions cosmétiques contenant de la phytosphingosine - Google Patents
Utilisation cosmétique de la phytosphingosine comme agent amincissant et compositions cosmétiques contenant de la phytosphingosine Download PDFInfo
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- WO2003074011A1 WO2003074011A1 PCT/FR2003/000656 FR0300656W WO03074011A1 WO 2003074011 A1 WO2003074011 A1 WO 2003074011A1 FR 0300656 W FR0300656 W FR 0300656W WO 03074011 A1 WO03074011 A1 WO 03074011A1
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- phytosphingosine
- agent
- cosmetic
- cosmetically acceptable
- cosmetic composition
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/06—Preparations for care of the skin for countering cellulitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Definitions
- phytosphingosine as a slimming agent and cosmetic compositions containing phytosphingosine
- phytosphingosine as a slimming agent and cosmetic compositions containing phytosphingosine.
- the present invention relates to a new cosmetic use of phytosphingosine as a slimming agent as well as cosmetic compositions containing phytosphingosine.
- Phytosphingosine has the following formula: Its molecular formula is C 18 H39 O 3 and its CAS number is as follows: RN 100,000 403-19-8. This product is also known under the name:
- phytosphingosine is a commercial product which corresponds to one of the three sphingoid bases naturally present in the skin, phytosphingosine being present in the stratum corneum.
- Applications of phytosphingosine and its salts and, more particularly its hydrochloride, are already known in the field of dermatology. Indeed, phytosphingosine is essentially known for its antimicrobial activity as well as for its activity as a "second messenger", an application which results in a reduction in the sensitivity of the skin. More specifically, phytosphingosine is known for its activity in the treatment of acne, for its activity of inhibiting the growth of microorganisms on the skin and for reducing various inflammatory phenomena observed on the skin.
- the inventors of the present invention have now discovered, quite surprisingly, a new use of phytosphingosine as well as its cosmetically acceptable salts, in particular its hydrochloride, as a slimming agent. They have by elsewhere highlighted that this new use was linked, at least partially, to the perfectly unexpected property of phytosphingosine and its salts, of promoting the synthesis of leptin by the adipocytes of the skin. Furthermore, continuing their studies in this field, the inventors of the present invention have also demonstrated that a certain number of combinations of phytosphingosine or of its cosmetically acceptable salts prove to be particularly advantageous in these new uses.
- human leptin or human protein OB
- OB human protein OB
- It is a protein secreted by the adipocyte which informs the brain of the state of fat stores. It acts through membrane receptors located in particular at the level of the hypothalamus.
- leptin triggers a satiety phenomenon causing a decrease in food intake and decreasing the frequency of food intake.
- the leptin produced by the adipose tissue will inhibit food intake and stimulate energy expenditure. It will therefore oppose excessive weight gain.
- this protein is a regulator of the adipose mass, the primary role of which is to inhibit the deposition of excess adiposity.
- the role of local regulation played by leptin is well known
- Leptin on the one hand suppresses the expression of certain genes leading to the accumulation of lipids (differentiation genes), and this without the participation of the brain.
- leptin induces lipolysis directly on the adipocytes. This has been observed on mouse adipocytes in vitro (see In vitro Lipolytic Effect of Leptin on Mouse Adipocytes: Evidence for a possible Autocrine / Paracrine Rbal of Leptin, G. Fr ⁇ hbeck, M. Aguado, JA Martinez, Biochemical and Biophysical Research communications 1997: 240, p. 590-594).
- the effect of leptin on lipolysis of adipocytes is specific and operates via receptors present in white adipose tissue.
- Leptin transforms estrone from the bloodstream (a hormone that increases lipid deposition) into oleyl-estrone which is considered to be a "slimming" factor.
- the appearance of this factor causes generalized lipolysis and thermogenesis (see Leptin enhances the synthesis of oleyl-estrone from estrone in white adipose tissue, M. Esteve, I Virgili, H. Aguilar, F. Balada, JA Fernandez-Lopez, W. Remesar, M. Alemany, Eur J. Nutr. 1999, 38, p. 99-104).
- Administered to obese or normal rats oleyl-estrone causes a loss of fat mass.
- the present invention relates according to a first aspect to a new cosmetic use of phytosphingosine or of a cosmetically acceptable salt thereof, in particular its hydrochloride, as a slimming agent for the manufacture of a cosmetic composition intended to reduce subcutaneous fatty overloads.
- the invention relates to a new cosmetic use of phytosphingosine or one of its cosmetically acceptable salts, in particular its hydrochloride, as an active agent stimulating the synthesis of leptin by adipocytes, for the manufacture of '' a cosmetic composition intended to reduce fatty overloads under the skin.
- the invention relates to a cosmetic treatment method intended to obtain a slimming effect on the human body, according to which an effective amount of a cosmetic composition containing is applied to the parts of the body where said effect is sought.
- a cosmetic treatment method intended to obtain a slimming effect on the human body, according to which an effective amount of a cosmetic composition containing is applied to the parts of the body where said effect is sought.
- At least one cosmetically acceptable lipolytic agent will be chosen from the group consisting of radenosine-3 ', 5'-cydic monophosphate (cAMP) and its derivatives, the activators of the enzyme adenylate cyclase and the agents phosphodiesterase enzyme inhibitors.
- an activating agent for adenylate cyclase advantageously choose forskolin or a plant extract containing it, such as an extract of Coleus forskohlii or Plectranthus barbatus, or an extract of the plant Tephrosia purpurea.
- a phosphodiesterase inhibiting agent it is possible to use a xanthine such as 3-isobutyl-1-methyl-xanthine or IBMX, caffeine or theophilline.
- Cosmetic compositions containing such associations which are new in themselves, constitute the fourth aspect of the present invention. It is these compositions as described below which will preferably be used in all the cosmetic applications targeted by the present invention.
- the present invention relates to a cosmetic composition, in particular intended to reduce fatty overloads under the skin, characterized in that it contains, as active agent, - phytosphingosine or one of its cosmetically acceptable salts, in particular its hydrochloride and
- At least one cosmetically acceptable lipolytic agent chosen from the group consisting of cAMP and its cosmetically acceptable derivatives, agents activating the adenylate cyclase enzyme and agents inhibiting the phosphodiesterase enzyme, in a cosmetically acceptable vehicle.
- phytosphingosine or one of its cosmetically acceptable salts, in particular its hydrochloride is contained in the composition cosmetic at a concentration of between 0.001% and 1% and preferably between 0.05% and 0.5% by weight relative to the total weight of said composition.
- the cosmetic composition also contains at least one active lipolytic agent chosen from the group consisting of cAMP and its lipolytic derivatives, agents activating the adenylate cyclase enzyme and agents inhibiting the phosphodiesterase enzyme.
- the cAMP or its derivative will advantageously be used at a concentration of between 0.001% and 5% by weight relative to the total weight of the composition.
- a cAMP derivative one can choose any cosmetically acceptable cAMP derivative and in particular a salt or an acylated derivative, in particular a mono- or dibutyryl derivative.
- an activating agent for the adenylate cyclase enzyme forskolin or a plant extract containing it is advantageously chosen, preferably at a concentration of between 0.001% and 1% and preferably between 0.05 % and 0.25%, by weight relative to the total weight of the composition.
- extract containing forskolin it is preferable to choose an extract of Coleus forskohlii or Plectranthus barbatus.
- Such an extract can be obtained by an extraction process such as that described in international application WO 91/02516.
- an extract from the plant Tephrosia purpurea at a concentration of between 0.001% and 5%, preferably between 0.01% and 5%, by weight relative to the total weight of the composition.
- an extract can be obtained by an extraction process such as that described in international application WO 95/03780.
- the preferred compositions according to the invention contain a phosphodiesterase inhibiting agent, in particular a xanthine and, very particularly, 3-isobutyl-1-methyl-xanthine (IBMX), caffeine or theophillin, preferably at a concentration of between 0.001% and 10%, preferably between 0.01 and 1%, by weight relative to the weight of the composition.
- a phosphodiesterase inhibiting agent in particular a xanthine and, very particularly, 3-isobutyl-1-methyl-xanthine (IBMX), caffeine or theophillin
- compositions used according to the present invention which contain a combination of phytosphingosine or one of its salts with a lipolytic agent such as cAMP and its lipolytic derivatives, agents activating adenylate cyclase and agents inhibiting phosphodiesterase, prove to be particularly interesting because of the synergistic action of the two types of constituents.
- the concept that body fat can be regulated via secreting circulating factors is very interesting.
- the principle of the test is to control the secretion of leptin by adipocytes.
- a clone which has the capacity to accumulate large amounts of triglycerides has been isolated from an established line of 3T3 mouse preadipocytes. Lipolytic agents reduce this build-up. It therefore appeared relevant to test potential lipolytic agents on this line of 3T3 murine preadipocytes F442A.
- These preadipocytes (GREEN H. and KEHINDE O. - Spontaneous Heritable Changes Leading to Increased Adipose Conversion in 3T3 Cells, Cell Vol. 7, 105-113, 1976) can multiply and differentiate by presenting the morphological and biochemical phenotype characteristic of differentiated function of the mature adipocyte. When they are in exponential growth phase, they are fibroblastic in appearance, have an elongated shape and are very adherent to the support. At confluence when conditions allow, a very early morphological transition gives them a rounded shape.
- the cells then undergo a process of clonal amplification.
- increases in the activity of lipogenetic enzymes as well as increases in responses on the part of cells to hormones / factors affecting lipogenesis and lipolysis.
- the 3T3 F442A preadipocytes therefore constitute an excellent model for studying lipolysis due to the morphological and metabolic transformations acquired by the cells during their development program.
- Pairault J and Lasnier F Control of adipogenetic differentiation of 3T3 F442A cells by retinoic acid, dexamethasone and insulin: a topographie analysis J. cell Physiol. 1987, 132, 279-86).
- leptin is secreted into the culture medium since it is stored in adipocytes.
- 3T3 F442A cells the expression of the ob gene has been particularly studied (Leroy P et al, J. of Biol. Chem, 1996, vol 271 n ° 5, pp. 2365-2368, Considine RV et al - Horm. Res. 1996, 46: 249-256).
- the 3T3 F442A preadipocytes are seeded on D0 in 35 mm Petri dishes (Corning) and placed in the oven at 37 ° C. air-CO 2 atmosphere (95-5).
- the cells are cultured in a minimum essential Eagle medium modified according to Dulbecco (glucose 4.50 g / 1) (DMEM-GIBCO BRL) supplemented with 5% calf serum (SV) (BIOMEDIA ® ) and 5% serum from fetal calf (GIBCO) during the growth phase.
- DMEM-GIBCO BRL Dulbecco
- SV calf serum
- BIOMEDIA ® 5% serum from fetal calf
- the basic medium remains the same (DMEM) but is supplemented with 10% fetal calf serum (SVF) and insulin (5 ⁇ g / ml) (SIGMA).
- DMEM fetal calf serum
- SIGMA insulin (5 ⁇ g / ml)
- the medium is then changed at D9 and Dll.
- the secreted leptin is determined using an Elisa sandwich type technique using the Quantikine® M Mouse Leptin Immunoassay kit.
- This ELISA assay uses the recombinant mouse leptin, expressed in E.Coli and antibodies directed against the recombinant mouse leptin.
- the test uses an immunoenzymatic "sandwich" technique.
- the microplate wells are coated with a polyclonal antibody to mouse leptin.
- the bound leptin is then detected by an anti-mouse leptin antibody coupled to an enzyme, peroxidase.
- Substrate solution is then added to the wells. The enzymatic reaction leads to a blue solution which turns yellow after addition of a stop solution.
- the intensity of the color measured is proportional to the amount of leptin present.
- the optical density is read at 450 nm with a spectrophotometer.
- Quantikine M therefore makes it possible to determine relative mass values for natural mouse leptin.
- optical density measured at 450 nm is proportional to the amount of antibody fixed, itself proportional to the amount of leptin initially present.
- the results are expressed in pg / ml of leptin present in the cell supernatants.
- phytosphingosine induces an increase in the secretion of leptin by the adipocytes treated, an effect which is maximum at the concentration of 0.25 ⁇ g / ml. At this concentration, the increase is just over 18%.
- phytosphingosine hydrochloride is also responsible for stimulating leptin secretion: + 52% at 1 ⁇ g / mL and + 26% at 2 ⁇ g / mL and + 18% at 0.25 ⁇ g / mL.
- the results for the hydrochloride are reported in Table 2 below.
- phytosphingosine is capable of inducing in the fat cell 3T3-F442A, a model very close to the human adipocyte, an increase in the basal adipocyte secretion of leptin. Phytosphingosine is therefore capable of playing an important role in controlling the stability of fat mass.
- Example 2 Demonstration of the Interest of Combining Phytosphingosine with an Adenylate Cyclase Activator, Such as an Extract of Coleus forskohlii, for Promoting the Reduction of Lipogenesis in Murine Adipocytes in Culture.
- an Adenylate Cyclase Activator Such as an Extract of Coleus forskohlii, for Promoting the Reduction of Lipogenesis in Murine Adipocytes in Culture.
- adipocyte is associated within the adipose tissue, with an abundant extracellular matrix which also contains endothelial cells, capillaries, nerve fibers and fibroadipoblasts precursors.
- the mature adipocyte represents the phenotype of a cell resulting from the differentiation of an adipocyte precursor.
- the preadipocytes are present within the adipose tissue and can be recruited at all stages of life to generate new adipocytes: in the case of weight gain, there is an initial phase of increase in adipocyte volume up to reaching a critical point, then leading to the recruitment of new cells (Bjorntorp P., Int. J. Obesity, (1991) 15 67-81).
- the intrinsic capacity of preadipocytes to multiply and to differentiate into adipocytes plays a determining role in the development of fatty masses. Hyperplasia of these fibroblast-like cells leads to an increase in adipose tissue.
- mature adipocytes are treated with PB + PS.
- the culture medium conditioned by these adipocytes is brought into contact with preadipocytes, the maturation of which is followed by adipocytes.
- control cells at the start of the treatment begin to differentiate and undergo a certain number of changes: increase in volume, increase in the number and size of the lipid droplets, increase in the activity of lipogenetic enzymes, etc.
- G 3 PDH glycerol-3-phosphate dehydrogenase
- G 3 PDH is a water-soluble enzyme
- its activity is measured in the supernatant of the cell ground material in the presence of the appropriate substrates (NADH, TEA (triethanolamine) - EDTA, 50 mM, 1 mM). From the dosages, the specific activity is calculated.
- the treated cells are compared with the control cells.
- the G 3 PDH being the reflection the differentiation state of the cells, the greater its specific activity and the more the cells are differentiated and vice versa: the more the reserve of fat will be limited by the agent tested the more the activity of G 3 PDH will be weak.
- the average over three measurements related to a standard deviation gives the average specific activity, then the percentage of inhibition of the activity of G 3 PDH produced by the substances is calculated compared to the controls.
- the criteria for ensuring the quality of good anti-lipogenetic agents are on the one hand a percentage of inhibition of the enzyme greater than 50% and on the other hand raw data significantly different from the controls.
- adipocytes undergoing differentiation, not very mature adipocytes still called preadipocytes obtained on D7 of the protocol given in Example 1 are treated with medium conditioned by mature differentiated adipocytes treated or not with PB or PS and by the association PB + PS for 8 days with a change of environment on days D9 and Dll, as indicated in the protocol below.
- PB Plectranthus barbatus
- lot no. 0B2, INDENA The extract of Plectranthus barbatus (PB) (lot no. 0B2, INDENA) is titrated to 80% in forskolin, a molecule known to be an effector of adenylate cyclase (Seamon K. et al., PNAS USA, (1981) 78 3363-67).
- the concentration of PB used in the study is 25 ⁇ g / ml from a stock solution of 20 mg / ml in ethanol.
- the cell carpet is washed twice with PBS buffer and the cells are recovered by scraping in 25 mM buffer, TRIS - HCl, pH 7.5 containing 1 mM EDTA at 4 ° C.
- the cells are homogenized by grinding and centrifugation at 10,000 g for 10 minutes at 4 ° C.
- the protocol followed is summarized in the table below.
- the assay for G 3 PDH activity is carried out according to the method of Kozak and Jensen: Kozak and Jensen, 1974, J. Biol. Chem., 249, 7775-7781.
- G 3 PDH catalyzes the following reaction: Dihydroxyacetone phosphate + NADH, H + - glycerol 3 phosphate + NAD +
- the consumption of NADH as a function of time is measured by spectrophotometry (KONTRON) at 340 nm.
- KNTRON spectrophotometry
- ⁇ Abs / minute absorbance / minute
- the results are expressed in specific activity (AS), ie in nmoles of NADH transformed / min / mg of proteins.
- AS specific activity
- the total protein level is evaluated by the BCA method (Protein Assay Reagent-PIERCE LTD)
- G 3 PDH glycero-3-phosphate dehydrogenase
- association PS + PB causes between 74 and 79% inhibition of the activity of G 3 PDH
- association PS 1 ⁇ g / ml + PB 25 ⁇ g / ml even causes a slowdown in the lipogenesis of these preadipocytes during maturation slightly greater than the PB alone.
- adipocytes were analyzed by direct observation of the cells in the petri dishes, under a reverse phase microscope (Olympus BH2). Cells are considered to be differentiated by morphological analysis when they acquire a round outline and their cytoplasm is filled with lipid droplets. Conversely, a decrease in the quantity of lipid vacuoles associated with a more elongated form indicates a slowing down of this maturation.
- Figures 2, 3 and 4 show respectively: Figure 2: cells of a control culture on D7. In this culture, the cells are very little differentiated, there are few lipid vacuoles. This is the start of treatment.
- Figure 3 cells from a control culture on D21. The cells are loaded with lipid vacuoles.
- Figure 4 the cells of a culture treated by the association PB 25 ⁇ g / mL + PS 1 ⁇ g / mL
- phytosphingosine capable of stimulating the secretion of leptin, did not inhibit the massive action of PB on the destocking of lipids.
- D 0 start of treatment with Coleus extract (PB) and / or phytosphingosine (PS)
- D 6 to D 18 assays of the various parameters.
- glycerol expressed in ⁇ g / mL, by human adipocytes in culture, treated or not with 25 ⁇ g / mL of phytosphingosine, depending on the duration of culture
- FIGS. 5 and 6 show the evolution of the morphology of the cells under the conditions which have just been mentioned.
- FIG. 5 shows a control culture of human adipocytes on day D18.
- FIG. 6 shows a culture of human adipocytes on day D18, after treatment with the association of Coleus (25 ⁇ g / ml) with phytosphingosine (6ng / ml). It is clear that the phytosphingosine - Coleus association leads to a massive and visible destocking, with fewer and smaller lipid droplets.
- PPG-2 isoceteth-20 acetate 2%
- Poloxamer 407 0.50%
Abstract
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Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002477752A CA2477752A1 (fr) | 2002-03-01 | 2003-02-28 | Utilisation cosmetique de la phytosphingosine comme agent amincissant et compositions cosmetiques contenant de la phytosphingosine |
DE60313141T DE60313141T2 (de) | 2002-03-01 | 2003-02-28 | Kosmetische verwendung von phytosphingosin als schlankmacher und phytosphingosin enthaltende kosmetische zusammensetzungen |
EP03735763A EP1480601B1 (fr) | 2002-03-01 | 2003-02-28 | Utilisation cosmetique de la phytosphingosine comme agent amincissant et compositions cosmetiques contenant de la phytosphingosine |
AU2003238145A AU2003238145A1 (en) | 2002-03-01 | 2003-02-28 | Cosmetic use of phytosphingosine as slimming agent and cosmetic compositions comprising phytosphingosine |
US10/506,407 US7737186B2 (en) | 2002-03-01 | 2003-02-28 | Cosmetic use of phytosphingosine as slimming agent and cosmetic compositions comprising phytosphingosine |
JP2003572533A JP4681230B2 (ja) | 2002-03-01 | 2003-02-28 | フィトスフィンゴシンのスリミング剤としての化粧的使用、及び、フィトスフィンゴシンを含む化粧組成物 |
KR1020047012707A KR100955312B1 (ko) | 2002-03-01 | 2003-02-28 | 피토스핑고신의 체중감소제로서의 화장품적 용도 및피토스핑고신을 함유하는 화장품 조성물 |
HK05106902A HK1073264A1 (en) | 2002-03-01 | 2005-08-10 | Cosmetic use of phytosphingosine as a slimming agent and cosmetic compositions containing phytosphingosine |
US12/773,365 US8513310B2 (en) | 2002-03-01 | 2010-05-04 | Cosmetic use of phytosphingosine as slimming agent and cosmetic compositions comprising phytosphingosine |
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FR0202675 | 2002-03-01 | ||
FR0202675A FR2836630B1 (fr) | 2002-03-01 | 2002-03-01 | Utilisation cosmetique de la phytosphingosine comme agent amincissant et compositions cosmetiques contenant de la phytosphingosine |
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US10506407 A-371-Of-International | 2003-02-28 | ||
US12/773,365 Continuation US8513310B2 (en) | 2002-03-01 | 2010-05-04 | Cosmetic use of phytosphingosine as slimming agent and cosmetic compositions comprising phytosphingosine |
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WO2003074011A1 true WO2003074011A1 (fr) | 2003-09-12 |
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PCT/FR2003/000656 WO2003074011A1 (fr) | 2002-03-01 | 2003-02-28 | Utilisation cosmétique de la phytosphingosine comme agent amincissant et compositions cosmétiques contenant de la phytosphingosine |
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US (2) | US7737186B2 (fr) |
EP (1) | EP1480601B1 (fr) |
JP (1) | JP4681230B2 (fr) |
KR (1) | KR100955312B1 (fr) |
CN (1) | CN100376226C (fr) |
AT (1) | ATE359104T1 (fr) |
AU (1) | AU2003238145A1 (fr) |
CA (1) | CA2477752A1 (fr) |
DE (1) | DE60313141T2 (fr) |
FR (1) | FR2836630B1 (fr) |
HK (1) | HK1073264A1 (fr) |
WO (1) | WO2003074011A1 (fr) |
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JP7246605B2 (ja) * | 2018-01-09 | 2023-03-28 | 共栄化学工業株式会社 | 皮膚外用組成物 |
JP7082827B2 (ja) * | 2020-09-09 | 2022-06-09 | 丸善製薬株式会社 | 化粧料 |
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KR100371491B1 (ko) | 1999-07-27 | 2003-02-07 | 주식회사 두산 | 피부 보호용 크림조성물 |
JP4182183B2 (ja) | 1999-08-24 | 2008-11-19 | ディーエスエム アイピー アセッツ ビー.ブイ. | 痩身用皮膚化粧料 |
JP4430770B2 (ja) | 2000-01-07 | 2010-03-10 | 花王株式会社 | 皮膚弾力性改善剤 |
FR2810548A1 (fr) * | 2000-06-26 | 2001-12-28 | Oreal | Utilisation d'ergothioneine et/ou de ses derives comme agent anti-glycation |
US6572868B1 (en) * | 2000-07-25 | 2003-06-03 | Sandra E. Cope | Restructuring complex for cosmetic compositions |
US6372236B1 (en) * | 2000-10-18 | 2002-04-16 | Doosan Corporation | Cream composition for skin care |
-
2002
- 2002-03-01 FR FR0202675A patent/FR2836630B1/fr not_active Expired - Lifetime
-
2003
- 2003-02-28 US US10/506,407 patent/US7737186B2/en not_active Expired - Lifetime
- 2003-02-28 AT AT03735763T patent/ATE359104T1/de not_active IP Right Cessation
- 2003-02-28 CA CA002477752A patent/CA2477752A1/fr not_active Abandoned
- 2003-02-28 EP EP03735763A patent/EP1480601B1/fr not_active Expired - Lifetime
- 2003-02-28 JP JP2003572533A patent/JP4681230B2/ja not_active Expired - Lifetime
- 2003-02-28 CN CNB038050587A patent/CN100376226C/zh not_active Expired - Lifetime
- 2003-02-28 WO PCT/FR2003/000656 patent/WO2003074011A1/fr active IP Right Grant
- 2003-02-28 AU AU2003238145A patent/AU2003238145A1/en not_active Abandoned
- 2003-02-28 KR KR1020047012707A patent/KR100955312B1/ko active IP Right Grant
- 2003-02-28 DE DE60313141T patent/DE60313141T2/de not_active Expired - Lifetime
-
2005
- 2005-08-10 HK HK05106902A patent/HK1073264A1/xx not_active IP Right Cessation
-
2010
- 2010-05-04 US US12/773,365 patent/US8513310B2/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5578641A (en) * | 1993-04-20 | 1996-11-26 | Elizabeth Arden Co., Division Of Conopco, Inc. | Cosmetic composition |
WO1995003780A1 (fr) * | 1993-07-28 | 1995-02-09 | Parfums Christian Dior | Composition cosmetique ou pharmaceutique, notamment dermatologique, contenant un extrait de tephrosia, en particulier tephrosia purpurea |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2404641A3 (fr) * | 2009-08-28 | 2014-06-11 | ROVI Cosmetics International GmbH | Formule cosmétique pour la réduction de l'apparence extérieure de la cellulite ou de la peau d'orange |
Also Published As
Publication number | Publication date |
---|---|
CA2477752A1 (fr) | 2003-09-12 |
AU2003238145A1 (en) | 2003-09-16 |
ATE359104T1 (de) | 2007-05-15 |
KR100955312B1 (ko) | 2010-04-29 |
US8513310B2 (en) | 2013-08-20 |
JP4681230B2 (ja) | 2011-05-11 |
FR2836630B1 (fr) | 2004-07-09 |
JP2006505496A (ja) | 2006-02-16 |
US7737186B2 (en) | 2010-06-15 |
US20050107459A1 (en) | 2005-05-19 |
HK1073264A1 (en) | 2005-09-30 |
US20100233298A1 (en) | 2010-09-16 |
EP1480601B1 (fr) | 2007-04-11 |
FR2836630A1 (fr) | 2003-09-05 |
DE60313141D1 (de) | 2007-05-24 |
CN1638717A (zh) | 2005-07-13 |
DE60313141T2 (de) | 2007-12-20 |
KR20040095221A (ko) | 2004-11-12 |
EP1480601A1 (fr) | 2004-12-01 |
CN100376226C (zh) | 2008-03-26 |
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